1. Field of the Invention
The present invention relates to a novel method of producing an organosilylamine, and also relates to a novel organosilylamine. More specifically, the present invention relates to a novel method of producing an organosilylamine that contains a radiation-polymerizable functional group within the molecule, and also relates to a novel organosilylamine containing a radiation-polymerizable functional group within the molecule.
2. Description of the Prior Art
In an organosilylamine, the silicon-nitrogen bond contained within the molecule generally undergoes a deammonization reaction in the presence of water or a hydroxyl group to form a silicon-oxygen bond, and as a result, organosilylamines are widely used as silyl blocking agents for hydroxyl groups and the like, and as surface treatment agents and the like for inorganic oxides and inorganic substrates.
However, in almost all of the organosilylamines used for the above purposes, the organic functional group bonded to the silicon atom is a simple hydrocarbon-based organic functional group such as an alkyl group or a vinyl group, and very few organosilylamines are known in which other organic functional groups, including organic functional groups having polymerization reactivity such as radiation-polymerizability, are bonded to the silicon atom.
Although being typical compounds, organosilylamines are restricted in terms of the organic functional groups that can be introduced into the molecule, and therefore methods of producing the organosilylamines are also restricted. In other words, conventionally, a production method is used in which the organosilylamine is produced by a dehydrohalogenation reaction of the corresponding organohalosilane with ammonia, a primary amine or a secondary amine (see Patent References 1 to 3). However, with this method, synthesis of an organosilylamine having a functional group that exhibits favorable reactivity with amines is problematic. Furthermore, in the above method, the ammonia, primary amine or secondary amine that is used as a raw material, and ammonia in particular, has a high degree of toxicity and must be handled with considerable caution. Moreover, in the above reaction, following completion of the dehydrohalogenation reaction, by-products such as hydrogen halides and ammonium halides or hydrohalides of the primary amine or secondary amine, as well as residual ammonia, must be removed from the reaction system, and this process is complex. In other words, conventional methods of production could be improved in terms of productivity and safety.
It has been postulated that organosilylamines having a radiation (UV radiation) polymerizable group such as a methacryloyl group or acryloyl group as an organic functional group should enable the ready introduction of radiation-polymerizable groups at the terminals or surfaces of inorganic oxides such as silicone or silica, or at the surfaces of inorganic substrates, and as such, could be described as long-awaited surface treatment agents.
[Patent Reference 1] U.S. Pat. No. 3,927,057
[Patent Reference 2] U.S. Pat. No. 3,481,964
[Patent Reference 3] U.S. Pat. No. 4,617,078